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Synfacts 2008(4): 0339-0339  
DOI: 10.1055/s-2008-1042885
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Galbonolide B

Contributor(s): Philip Kocienski
P. J. Parsons*, L. Pennicott, J. Eshelby, M. Goessman, A. Highton, P. Hitchcock
The University of Sussex, Brighton, Pfizer Pharmaceuticals Limited, Sandwich and AstraZeneca, Macclesfield, UK
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

Galbonolide B is active against some pathogenic fungi. The Sussex synthesis ­elegantly installs the 1,6-stereogenic centers and the diene moiety in fragment C by means of an Ireland-Claisen rearrangement followed by a silicon-mediated 1,4-elimination. The creation of the macrocycle (J → K) by means of an intramolecular Claisen condensation is also noteworthy.